EP0523006B1 - Verfahren zum Bedrucken und photochemischen Stabilisieren von Polyesterfasermaterialien - Google Patents
Verfahren zum Bedrucken und photochemischen Stabilisieren von Polyesterfasermaterialien Download PDFInfo
- Publication number
- EP0523006B1 EP0523006B1 EP92810511A EP92810511A EP0523006B1 EP 0523006 B1 EP0523006 B1 EP 0523006B1 EP 92810511 A EP92810511 A EP 92810511A EP 92810511 A EP92810511 A EP 92810511A EP 0523006 B1 EP0523006 B1 EP 0523006B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- c5alkyl
- absorber
- c5alkoxy
- formula
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000007639 printing Methods 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 32
- 229920000728 polyester Polymers 0.000 title claims abstract description 18
- 239000000835 fiber Substances 0.000 title claims abstract description 17
- 239000000463 material Substances 0.000 title claims abstract description 13
- 230000000087 stabilizing effect Effects 0.000 title description 4
- 239000006096 absorbing agent Substances 0.000 claims abstract description 50
- 239000000986 disperse dye Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 230000003019 stabilising effect Effects 0.000 claims abstract 3
- -1 chloro, hydroxy Chemical group 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical group OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 239000012965 benzophenone Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 17
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- 150000001875 compounds Chemical class 0.000 description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000002947 alkylene group Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 4
- 229960003742 phenol Drugs 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000010023 transfer printing Methods 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 0 *c(cc1O)ccc1-c1nc(O*)nc(*)n1 Chemical compound *c(cc1O)ccc1-c1nc(O*)nc(*)n1 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- CCEHUZJNDSXPCB-UHFFFAOYSA-N 3,6-dihydroazepine-2,7-dione Chemical compound O=C1CC=CCC(=O)N1 CCEHUZJNDSXPCB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OSNDUYDDOHEKEE-UHFFFAOYSA-N azepane-2,7-dione Chemical compound O=C1CCCCC(=O)N1 OSNDUYDDOHEKEE-UHFFFAOYSA-N 0.000 description 2
- ODBPKBWAGSAZBE-UHFFFAOYSA-N benzo[f]isoindole-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)NC(=O)C3=CC2=C1 ODBPKBWAGSAZBE-UHFFFAOYSA-N 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- ZPLNASMNUBJSDR-UHFFFAOYSA-N isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1.C1=CC=C2C(=O)NC(=O)C2=C1 ZPLNASMNUBJSDR-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000010022 rotary screen printing Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000003799 water insoluble solvent Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- UKVGXELZQSJUTH-UHFFFAOYSA-N 2-(4,6-didecyl-1,3,5-triazin-2-yl)phenol Chemical compound CCCCCCCCCCC1=NC(CCCCCCCCCC)=NC(C=2C(=CC=CC=2)O)=N1 UKVGXELZQSJUTH-UHFFFAOYSA-N 0.000 description 1
- LNBSDTJULOKQCT-UHFFFAOYSA-N 2-(4,6-diethyl-1,3,5-triazin-2-yl)-4,5-dimethylphenol Chemical compound CCC1=NC(CC)=NC(C=2C(=CC(C)=C(C)C=2)O)=N1 LNBSDTJULOKQCT-UHFFFAOYSA-N 0.000 description 1
- VKFYRDQFUUWVSJ-UHFFFAOYSA-N 2-(4,6-dimethyl-1,3,5-triazin-2-yl)-4,5-dimethylphenol Chemical compound C1=C(C)C(C)=CC(O)=C1C1=NC(C)=NC(C)=N1 VKFYRDQFUUWVSJ-UHFFFAOYSA-N 0.000 description 1
- RJBNOOYPPQJCJT-UHFFFAOYSA-N 2-(4,6-dimethyl-1,3,5-triazin-2-yl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(C=2N=C(C)N=C(C)N=2)=C1 RJBNOOYPPQJCJT-UHFFFAOYSA-N 0.000 description 1
- DUUPYWGBKXYZIZ-UHFFFAOYSA-N 2-(4,6-dimethyl-1,3,5-triazin-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2N=C(C)N=C(C)N=2)=C1 DUUPYWGBKXYZIZ-UHFFFAOYSA-N 0.000 description 1
- OJADXDOGYHVWDN-UHFFFAOYSA-N 2-(4,6-dimethyl-1,3,5-triazin-2-yl)phenol Chemical compound CC1=NC(C)=NC(C=2C(=CC=CC=2)O)=N1 OJADXDOGYHVWDN-UHFFFAOYSA-N 0.000 description 1
- OFJFRCRFNOCFPW-UHFFFAOYSA-N 2-(4,6-dioctyl-1,3,5-triazin-2-yl)phenol Chemical compound CCCCCCCCC1=NC(CCCCCCCC)=NC(C=2C(=CC=CC=2)O)=N1 OFJFRCRFNOCFPW-UHFFFAOYSA-N 0.000 description 1
- IGFDJZRYXGAOKQ-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-ethoxyphenol Chemical compound OC1=CC(OCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 IGFDJZRYXGAOKQ-UHFFFAOYSA-N 0.000 description 1
- UUINYPIVWRZHAG-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 UUINYPIVWRZHAG-UHFFFAOYSA-N 0.000 description 1
- VQTWLUCKWLXPPS-UHFFFAOYSA-N 2-(4,6-dipropyl-1,3,5-triazin-2-yl)phenol Chemical compound CCCC1=NC(CCC)=NC(C=2C(=CC=CC=2)O)=N1 VQTWLUCKWLXPPS-UHFFFAOYSA-N 0.000 description 1
- YSSYJGUBRBPHBC-UHFFFAOYSA-N 2-(4,6-ditert-butyl-1,3,5-triazin-2-yl)phenol Chemical compound CC(C)(C)C1=NC(C(C)(C)C)=NC(C=2C(=CC=CC=2)O)=N1 YSSYJGUBRBPHBC-UHFFFAOYSA-N 0.000 description 1
- LQKSRVSHDGNXFJ-UHFFFAOYSA-N 2-[4,6-bis(2-methylsulfanylethyl)-1,3,5-triazin-2-yl]phenol Chemical compound CSCCC1=NC(CCSC)=NC(C=2C(=CC=CC=2)O)=N1 LQKSRVSHDGNXFJ-UHFFFAOYSA-N 0.000 description 1
- KGTOEEDRVZXMMU-UHFFFAOYSA-N 2-[4,6-bis[2-(butylamino)ethyl]-1,3,5-triazin-2-yl]phenol Chemical compound CCCCNCCC1=NC(CCNCCCC)=NC(C=2C(=CC=CC=2)O)=N1 KGTOEEDRVZXMMU-UHFFFAOYSA-N 0.000 description 1
- LFBZYKVGLHJEKM-UHFFFAOYSA-N 2-[4,6-bis[2-(dimethylamino)ethyl]-1,3,5-triazin-2-yl]phenol Chemical compound CN(C)CCC1=NC(CCN(C)C)=NC(C=2C(=CC=CC=2)O)=N1 LFBZYKVGLHJEKM-UHFFFAOYSA-N 0.000 description 1
- SXFBMPJPLXXFFN-UHFFFAOYSA-N 2-[4,6-di(heptadecyl)-1,3,5-triazin-2-yl]phenol Chemical compound CCCCCCCCCCCCCCCCCC1=NC(CCCCCCCCCCCCCCCCC)=NC(C=2C(=CC=CC=2)O)=N1 SXFBMPJPLXXFFN-UHFFFAOYSA-N 0.000 description 1
- JSZKRKKTFWXMQZ-UHFFFAOYSA-N 2-[4,6-di(nonyl)-1,3,5-triazin-2-yl]phenol Chemical compound CCCCCCCCCC1=NC(CCCCCCCCC)=NC(C=2C(=CC=CC=2)O)=N1 JSZKRKKTFWXMQZ-UHFFFAOYSA-N 0.000 description 1
- QJVKAVMBANMJKY-UHFFFAOYSA-N 2-[4-(2-hydroxy-4-methoxyphenyl)-6-octoxy-1,3,5-triazin-2-yl]-5-methoxyphenol Chemical compound N=1C(OCCCCCCCC)=NC(C=2C(=CC(OC)=CC=2)O)=NC=1C1=CC=C(OC)C=C1O QJVKAVMBANMJKY-UHFFFAOYSA-N 0.000 description 1
- WKVMOQXBMPYPGK-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].OC(=O)CN(CC(O)=O)CC(O)=O WKVMOQXBMPYPGK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NUBZGQQHTISWLZ-UHFFFAOYSA-N 4-chloro-2-(4,6-dimethyl-1,3,5-triazin-2-yl)phenol Chemical compound CC1=NC(C)=NC(C=2C(=CC=C(Cl)C=2)O)=N1 NUBZGQQHTISWLZ-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- BWZQLVJQEQFOLU-UHFFFAOYSA-N 4-tert-butyl-2-(4,6-dimethyl-1,3,5-triazin-2-yl)phenol Chemical compound CC1=NC(C)=NC(C=2C(=CC=C(C=2)C(C)(C)C)O)=N1 BWZQLVJQEQFOLU-UHFFFAOYSA-N 0.000 description 1
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BRJVGSBQJZCIIN-UHFFFAOYSA-N OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCCOCC.OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCC Chemical compound OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCCOCC.OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCC BRJVGSBQJZCIIN-UHFFFAOYSA-N 0.000 description 1
- SIQVNKSLWCLUBH-UHFFFAOYSA-N OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCCC.OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCCOCCOCC Chemical compound OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCCC.OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCCOCCOCC SIQVNKSLWCLUBH-UHFFFAOYSA-N 0.000 description 1
- XDLLDYCBXVKOHX-UHFFFAOYSA-N OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCCOCC.OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCC Chemical compound OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCCOCC.OC1=C(C=CC(=C1)OCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCC)O)OCCOCC XDLLDYCBXVKOHX-UHFFFAOYSA-N 0.000 description 1
- SNFQFCNAPMWWSH-UHFFFAOYSA-N OC1=C(C=CC(=C1)OCCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCCC)O)OCCOC.OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCCC Chemical compound OC1=C(C=CC(=C1)OCCC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OCCC)O)OCCOC.OC1=C(C=CC(=C1)OC)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC)O)OCCOCCC SNFQFCNAPMWWSH-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- AAAUMZZBNYAFHL-UHFFFAOYSA-N nitro nitroformate Chemical compound [O-][N+](=O)OC(=O)[N+]([O-])=O AAAUMZZBNYAFHL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000007651 thermal printing Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65112—Compounds containing aldehyde or ketone groups
Definitions
- the present invention relates to a method for printing and photochemically stabilizing polyester fiber materials with disperse dyes.
- the present invention is therefore based on the object of providing a method for printing polyester fibers which makes it possible to stabilize polyester fibers photochemically and to increase the light fastness of the printing inks applied to these fiber materials.
- the present invention accordingly relates to a process for printing and photochemically stabilizing polyester fiber materials with disperse dyes and subsequent heat treatment of these materials, which is characterized in that the fiber is printed with an aqueous printing paste which, in addition to the disperse dye, contains a UV absorber.
- UV absorbers are suitable for the method according to the invention Have sublimation resistance up to 165 ° C.
- substituents R, R1, R2 and R3 represent an alkyl group, it can be straight-chain or branched.
- alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n- Octyl, isooctyl, n-nonyl, isononyl, n-dodecyl, heptadecyl or octadecyl.
- C1-C5alkoxy or C1-C5alkylthio are e.g. B. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec.-butoxy, tert.-butoxy, pentoxy, isopentoxy, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec.-butylthio, tert.-butylthio, Pentylthio, isopentylthio or tert. Pentylthio.
- Examples of monoalkylamino are monomethyl, monoethyl, monopropyl, monoisopropyl, monobutyl or monopentylamino.
- Examples of dialkylamino are dimethyl-, methylethyl- or diethylamino.
- Halogen means for example fluorine, bromine or preferably chlorine.
- R7 C1-C5-alkoxy and R8 and R9 independently of one another are tolyl or xylyl.
- UV absorbers of the formula (3) are preferred, in which R7 is C1-C5alkoxy and R8 and R9 are each phenyl.
- Suitable compounds of the formulas (1), (2) and (3) are, for example 2- (2'-hydroxy-5'-methylphenyl) -4,6-dimethyl-s-triazine; F. 131 ° C: 2- (2'-Hydroxy-3 ', 5'-dimethylphenyl) -4,6-dimethyl-s-triazine: mp 177 ° C: 2- (2'-Hydroxy-4 ', 5'-dimethylphenyl) -4,6-dimethyl-s-triazine: ⁇ 349 »m: T 48%: 2- (2'-Hydroxy-4 ', 5'-dimethylphenyl) -4,6-diethyl-s-triazine: mp 98 ° C: 2- (2'-Hydroxy-5'-chlorophenyl) -4,6-dimethyl-s-triazine: mp 160 ° C: 2- (2'-hydroxyphenyl) -4,6-
- the substituents R11 and R12 in the meaning of C1-C10alkyl or C1-C20alkyl can be straight-chain or branched, e.g. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, tert.pentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, n-dodecyl, heptadecyl, octadecyl or eicosyl.
- R11 and R12 mean C6-C10Aryl, then it can be a mono- or bicyclic aromatic radical such as phenyl or naphthyl.
- R11 and R12 mean e.g. Benzyl, phenethyl, ⁇ -methylphenethyl or ⁇ , ⁇ -dimethylbenzyl.
- Steep R11 and R12 are C5-C8cycloalkyl, it can be cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
- R12 as C2-C17 alkenyl radicals are, for example, vinyl, allyl, 1-propenyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-decenyl, 3,6,8-decatrienyl or 2-heptadecenyl.
- R12 represents C8-C10 aralkenyl, it can be styryl or cinnamyl.
- R11 and R12 are connected to each other and R11 is unsubstituted or substituted by C1-C5alkyl methylene, then, with the meanings given above of R12 instead of the dioxo, the corresponding oxo compounds are formed.
- Acyl means C1-C5 alkanoyl, such as formyl, acetyl, propionyl, acryloyl, methacryloyl or benzoyl.
- the compounds of the formulas (1), (2) and (3) are known and can be prepared in a manner known per se, for example by heating an amidine and an o-hydroxybenzene carboxylic acid ester, preferably in an approximate molar ratio of 2: 1 in boiling , organic solvents [cf. US-A-3,896,125 and Helv. Chim. Acta 55 , 1566-1595 (1972)].
- the compounds of formula (5) can be prepared by methods known per se, e.g. in US-A-3,468,938, US-A-3,696,077 and US-A-4,698,064, respectively.
- Some of the compounds of the formula (4) are known or represent new compounds.
- the new compounds can be prepared by processes known per se, for example by reacting a corresponding 2- (2 ') substitutable in the 3'- or 5'-position.
- -Hydroxyphenyl) -benzotriazole compound with the N-methylol compound of a carboxamide or urethane (cf. US-A-4 077 971).
- UV absorbers that are suitable for the present invention are used as aqueous dispersions.
- the dispersions can also contain other additional components such as nonionic surfactants, further anionic and / or nonionic compounds, commercially available antifoams, preservatives and antifreezes.
- dispersions are expediently prepared by treating the UV absorbers of the formulas (1), (2), (3), (4) or (5) with a dispersant, e.g. pastes the acidic ester of formula (6) and water in a mixer and after any addition of the desired additional components such as nonionic surfactants, further anionic and / or nonionic compounds including the anti-foaming agents, preservatives and antifreezing agents, for 1 to 30, preferably 1 to 10 hours dispersed.
- the dispersion is advantageously carried out by the action of high shear forces, e.g. by grinding in a ball, sand or pearl mill. After grinding, an aqueous solution of a commercially available stabilizing or thickening agent and, if desired, water can be added, followed by stirring until uniform.
- the UV absorbers are added to the printing pastes in the form of their aqueous dispersions.
- the printing paste contains the corresponding UV absorber in amounts of 0.5 to 8%, preferably 1 to 2%, based on the weight of the printing paste.
- Linear polyester fibers are to be understood as synthetic fibers which e.g. can be obtained by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) cyclohexane, as well as copolymers of terephthalic and isophthalic acid and ethylene glycol.
- the linear polyester used almost exclusively in the textile industry so far consists of terephthalic acid and ethylene glycol.
- Acid-modified polyester fibers are, for example, polycondensation products of terephthalic acid or isophthalic acid, ethylene glycol and 1,2-dihydroxy-3- or 1,3-dihydroxy-2- (3-sodium sulfopropoxy) propane, 2,3-dimethylol-1- (sodium sulfopropoxy) - butane, 2,2-bis (3-sodium sulfopropoxyphenyl) propane or 3,5-dicarboxybenzenesulfonic acid or sulfonated terephthalic acid, sulfonated 4-methoxybenzenecarboxylic acid or sulfonated diphenyl-4,4'-dicarboxylic acid.
- the disperse dyes are water-insoluble to sparingly soluble dyes of various classes, for example nitro dyes, amino ketone dyes, ketone imine dyes, methine dyes, nitrodiphenyl dyes, quinoline dyes and in particular anthraquinone or azo dyes such as monoazo or disazo dyes. It is also possible to use mixtures of different disperse dyes.
- aqueous preparation which contains the dye (or dye mixtures) which is insoluble to poorly soluble in water.
- Suitable aqueous preparations of this type are, in particular, those described in DE-A-2,850,482.
- the amount of dyes to be added to the printing pastes depends on the desired color strength; In general, amounts of 0.01 to 15, preferably 0.02 to 10 percent by weight, based on the textile material used, have proven successful.
- the printing pastes advantageously contain acid-stable thickeners, preferably of natural origin such as ground flour derivatives, in particular sodium alginate, alone or in a mixture with modified cellulose, in particular with preferably 20 to 25 percent by weight carboxymethyl cellulose.
- the printing pastes can also contain acid donors such as butyrolactone or sodium hydrogen phosphate, preservatives, sequestering agents, emulsifiers, water-insoluble solvents, oxidizing agents or deaerating agents.
- Suitable preservatives are, above all, formaldehyde-releasing agents, such as, for example, paraformaldehyde and trioxane, especially aqueous, approximately 30 to 40% by weight formaldehyde solutions, and sequestering agents, for example sodium nitrilotriacetic acid, sodium ethylenediaminetetraacetic acid, especially sodium polymethaphosphate, in particular sodium hexamethaphosphate, as emulsifiers especially adducts of an alkylene oxide and a fatty alcohol, especially an adduct of oleyl alcohol and ethylene oxide, as water-insoluble solvents, high-boiling, saturated hydrocarbons, especially paraffins with a boiling range of about 160 to 210 ° C (so-called mineral spirits), as an oxidizing agent, for example an aromatic nitro compound , especially an aromatic mono- or dinitrocarboxylic acid or sulfonic acid, which is optionally present as an alkylene oxide adduct,
- the printing paste is applied over the entire surface or in places directly to the fiber material
- printing machines of a conventional type e.g. Gravure printing, rotary screen printing and flat film printing machines can be used appropriately.
- the fiber material is dried at temperatures up to 150 ° C., preferably 80 ° to 120 ° C.
- the prints are also finished in the usual way by rinsing with water and can optionally be cleaned by additional cleaning in an alkaline medium under reductive conditions, e.g. be made with sodium dithionite. In the latter case, the printing stains are again rinsed and dried.
- the present method is also suitable for transfer printing.
- the printing paste is applied over the entire surface, preferably in the form of a pattern, to the intermediate carrier, printing presses of conventional design, e.g. Rotary screen printing and gravure printing machines can be used appropriately.
- the intermediate carrier used in the transfer printing process is expediently a flexible, preferably spatially stable tape, a strip or a film with a smooth surface.
- the intermediate carrier should be heat-stable and inert, ie should have no affinity for the various components of the printing paste. It can consist of various materials, such as metal, such as an aluminum or steel foil, plastic, paper or a textile fabric, which can optionally be coated with a film of vinyl resin, ethyl cellulose or polyurethane resin. For cost reasons, primarily paper webs are used.
- the printed intermediate carrier is dried at about 80 to 150 ° C., in particular 80 to 120 ° C., for about 5 to 20 seconds.
- the actual transfer printing is carried out discontinuously on a press or continuously on a conventional thermal printing system at 160 to 250 ° C., in particular 190 to 220 ° C.
- the contact time is dependent on the set temperature and is between 20 and 60, preferably 30 and 45 seconds at 230 ° C. and is carried out using pressure, the dye being transferred from the intermediate carrier to the fiber material.
- the printed fiber material is separated from the intermediate carrier.
- no after-treatment is required, i.e. generally neither steaming to fix the dye, nor washing to improve fastness properties.
- the present process can be used to produce vivid, true-to-color and rub-fast prints with good white fond of the goods, which are characterized by high lightfastness of the prints and stability of the fiber material.
- a strong, pattern-like print is obtained on the polyester fabric on a white background with good levelness, good fastness properties and with sharp contours.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyesters Or Polycarbonates (AREA)
- Printing Plates And Materials Therefor (AREA)
- Treatment Of Fiber Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2086/91 | 1991-07-12 | ||
| CH208691 | 1991-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0523006A1 EP0523006A1 (de) | 1993-01-13 |
| EP0523006B1 true EP0523006B1 (de) | 1995-11-29 |
Family
ID=4225570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92810511A Expired - Lifetime EP0523006B1 (de) | 1991-07-12 | 1992-07-03 | Verfahren zum Bedrucken und photochemischen Stabilisieren von Polyesterfasermaterialien |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0523006B1 (ja) |
| JP (1) | JPH05209374A (ja) |
| AT (1) | ATE130883T1 (ja) |
| BR (1) | BR9202579A (ja) |
| CA (1) | CA2073580A1 (ja) |
| DE (1) | DE59204472D1 (ja) |
| DK (1) | DK0523006T3 (ja) |
| ES (1) | ES2080473T3 (ja) |
| GR (1) | GR3018250T3 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0657577A1 (de) * | 1993-12-06 | 1995-06-14 | Ciba-Geigy Ag | Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten oder bedruckten Polyesterfasermaterialien |
| WO1996029302A1 (en) * | 1995-03-17 | 1996-09-26 | Ciba Specialty Chemicals Holding Inc. | Liposomogenic uv absorbers |
| EP0864687A3 (de) * | 1997-03-11 | 1999-11-24 | Ciba SC Holding AG | Verfahren zur Verbesserung der photochemischen Stabilität von Färbungen und Drucken auf Polyesterfasern |
| JP2009030214A (ja) * | 2007-07-27 | 2009-02-12 | Senka Kk | 繊維製品の耐光堅牢度向上剤及び耐光堅牢度向上方法 |
| JP5072496B2 (ja) * | 2007-09-11 | 2012-11-14 | 小松精練株式会社 | リサイクル用のぼり旗の脱色方法およびのぼり旗のリサイクル方法 |
| DE102007046745A1 (de) * | 2007-09-28 | 2009-04-02 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dispersionsfarbstoff und/oder UV-Absorber enthaltende Präparationen |
| ES2463674T3 (es) | 2009-01-19 | 2014-05-28 | Basf Se | Pigmentos negros orgánicos y su preparación |
| DE102011082078A1 (de) * | 2011-09-02 | 2013-03-07 | Carl Stahl Gmbh & Co. Kg | Verfahren zum Bedrucken eines Gurtbands |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126588C (ja) * | 1961-06-16 | |||
| DE3417782A1 (de) * | 1983-05-23 | 1984-11-29 | Sandoz-Patent-GmbH, 7850 Lörrach | Faerbereihilfsmittel |
| US4775386A (en) * | 1986-05-05 | 1988-10-04 | Ciba-Geigy Corporation | Process for photochemical stabilization of undyed and dyed polyamide fibre material and blends thereof with other fibres: copper complex and light stabilizer treatment |
| US4831068A (en) * | 1987-02-27 | 1989-05-16 | Ciba-Geigy Corporation | Process for improving the photochemical stability of dyeings on polyester fibre materials |
| DE58906867D1 (de) * | 1988-05-31 | 1994-03-17 | Ciba Geigy | Wässrige Dispersion von 2-(2'-Hydroxyphenyl-)benzotriazolen. |
| ES2074688T5 (es) * | 1990-07-23 | 1998-11-01 | Ciba Geigy Ag | Dispersion acuosa de absorbentes de uv poco solubles. |
-
1992
- 1992-07-03 ES ES92810511T patent/ES2080473T3/es not_active Expired - Lifetime
- 1992-07-03 DK DK92810511.3T patent/DK0523006T3/da active
- 1992-07-03 AT AT92810511T patent/ATE130883T1/de not_active IP Right Cessation
- 1992-07-03 EP EP92810511A patent/EP0523006B1/de not_active Expired - Lifetime
- 1992-07-03 DE DE59204472T patent/DE59204472D1/de not_active Expired - Fee Related
- 1992-07-10 JP JP4206280A patent/JPH05209374A/ja active Pending
- 1992-07-10 BR BR929202579A patent/BR9202579A/pt not_active IP Right Cessation
- 1992-07-10 CA CA002073580A patent/CA2073580A1/en not_active Abandoned
-
1995
- 1995-11-30 GR GR950403168T patent/GR3018250T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE130883T1 (de) | 1995-12-15 |
| EP0523006A1 (de) | 1993-01-13 |
| BR9202579A (pt) | 1993-03-16 |
| JPH05209374A (ja) | 1993-08-20 |
| GR3018250T3 (en) | 1996-02-29 |
| CA2073580A1 (en) | 1993-01-13 |
| ES2080473T3 (es) | 1996-02-01 |
| DK0523006T3 (da) | 1995-12-27 |
| DE59204472D1 (de) | 1996-01-11 |
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